Classifications

• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0601—Acyclic or carbocyclic compounds
  • G03G5/0605—Carbocyclic compounds
  • G03G5/0607—Carbocyclic compounds containing at least one non-six-membered ring
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0601—Acyclic or carbocyclic compounds
  • G03G5/0605—Carbocyclic compounds
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0601—Acyclic or carbocyclic compounds
  • G03G5/0612—Acyclic or carbocyclic compounds containing nitrogen
  • G03G5/0614—Amines
  • G03G5/06142—Amines arylamine
  • G03G5/06144—Amines arylamine diamine
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
  • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
  • G03G5/02—Charge-receiving layers
  • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
  • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
  • G03G5/0601—Acyclic or carbocyclic compounds
  • G03G5/0618—Acyclic or carbocyclic compounds containing oxygen and nitrogen

Definitions

• Deposited marking material can thenbe either permanently fixed to the surface of the sensitive element byknown means such as heat, pressure, solventvapor, or the like, or transferred to a second element to which it can similarly be fixed. Likewise, the electrostatic charge pattern can be transferred to a second element'and developed there.
• Various-photoconductive insulating materials have been employed in the manufacture of electrophotographic elements. For example, vapors of selenium and vapors of selenium alloys deposited on a suitable sup port and particles of photoconductive zinc oxide held in a resinous, film-forming binder have found wide application inthe present-day document copying applicatrons.
• Typical of these organic photoconductors are the triphenylamines and the triarylmethane leuco bases.
• Optically clear photoconductor-containing elements hav ing desirable electrophotographic properties can be especially useful in electrophotography. Such electrophotographic elements can be exposed through a transparent base if desired, thereby providing unusual flexibility inequipment design.
• Such compositions when coated as a film or layer on a suitable support, also yield an element which is reusable; that is, it can be used to form subsequent images after residual toner from prior images has been removed by transfer and/or cleaning.
• An additional object is to provide a novel class of chemical compounds.
• Useful methane derivatives include a. alkylbis( N ,N-dialkylaminoaryl )methane b. cycloalkylbis(N,N-dialkylaminoaryl)methane and c. cycloalkenylbis(N,N-dialkylaniinoaryl)methane.
• the aryl moiety in the above described compounds can be further substituted by various groups including alkoxy having one to eight carbon atoms such as me thoxy, ethoxy, propoxy, butoxy, etc., hydroxy, halogen such as chlorine, bromine, etc.
• the alkyl groups of these compounds generally contain one to eighteen carbon atoms and include substituted alkyl groups.
• the cycloalkyl groups and the cycloalkenyl groups contain generally four to eight carbon atoms in the cyclic nucleusand may be further substituted by other substituents such as those described in the follow ing paragraphs.
• diarylmethanes and triarylmethanes have exhibited photoconductive properties when used as photoconductors in electrophotographic elements; Typical of these are the leuco base of malachite green, bis(4-dimethylaminophenyl)- phenylmethane and bis(4- dimethylaminophenyl)methane as described in British Pat. Nos. 984,965 and 980,879. Also, diarylmethane compounds have beenused'as activators for zinc oxide photoconductors. Such uses are described in British Pat. No. 1,141,666.
• the photoconductors described herein haveenhanced speed and/or stability over those photoconductors described in the prior art.
• substantial increases in speed are obtained compared to speeds attainable with many other closely related compounds which do not have the central methyl carbon atom substituted by the groups set forth above.
• These increases in speed are observed when the photoconductoris incorporated into a coating composition, coated onto a support and the coating accepts a suitable potential (e.g., 500-600 volts).
• the relative speed of the coating is determined on the basis of the reciprocal of the exposure required to reduce the potential of the surface charge to volts (toe speed).
• toe speed is known in the photographic art with ref erence to H and D curves.
• the term refers to corresponding curves resulting from exposure plotted against voltage.
• the reduction of the surface potential to 100 volts or below is significant in that it represents a requirement for suitable broad area development of an electrostatic image.
• the relative speed at 100 volts is a measure of the ability to produce and hence to develop or otherwise utilize the electrostatic latent image.
• the surface potential frequently does not drop to or below 100 volts and therefore no speed can be assigned to such a composition.
• the surface potentials of such resultant compositions usually drop below 100 volts, and thus, a definite speed can ,be ascertained. However, these speeds are improved when the photoconductors of this invention are employed.
• R R R and R are each lower aliphatic alkyl groups having one to 18 carbon atoms such as a methyl group, a propyl group, an ethyl group, a pentyl group, a hexyl group, an isobutyl group, a 3-methylpentyl group, an octyl group, etc;
• R and R each represent any of the following groups l. a lower aliphatic alkyl having one to 18 carbon atoms typically including those set forth above for R1, R2, R3 and I 2. a lower alkoxy having one to 18 carbon atoms,
• R represents any of the following groups. 1. an aliphatic alkyl group having one to 18 carbon atoms, e.g., methyl, ethyl, propyl, butyl, isobutyl, octyl, dodecyl, etc., including a substituted alkyl group having one to 18 carbon atoms such as a. alkoxyalkyl, e.g., ethoxypropyl, methoxybutyl,
• aryloxyalkyl e.g., phenoxyethyl, naphthoxymethyl, phenoxypentyl, etc.
• aminoalkyl e.g., aminobutyl, aminoethyl
• hydroxyalkyl e.g., hydroxypropyl, hydroxyoctyl
• aralkyl e.g., benzyl, phenethyl, w, w-diphenylalkyl, etc.
• alkylaminoalkyl e.g., methylaminopropyl, methylaminoethyl, etc., and also including dialkylaminoalkyl, e.g., diethylaminoethyl, dimethylaminopropyl, propylaminooctyl, etc.,
• arylaminoalkyl e.g., phenylaminoalkyl, diphenylaminoalkyl, N-phenyl-N- ethylaminopentyl, N-phenyl-N-ethylaminohexyl, naphthylaminomethyl, etc.
• nitroalkyl e.g., nitrobutyl, nitroeth'yl, nitropentyl, etc.
• cyanoalkyl e.g., cyanopropyl, cyanobutyl, cyanoethyl, etc.
• haloalkyl e.g., chloromethyl, bromopentyl, chlorooctyl, etc.
• a cycloalkyl group having four to eight carbon atoms in the cyclic nucleus e.g., cyclobutyl, cyclohexyl, cyclopentyl, etc., including a substituted cycloalkyl group such as a. alkoxycycloalkyl, e.g., ethoxycyclohexyl, me-
• aryloxycycloalkyl e.g., phenoxycyclohexyl, naphthoxycyclohexyl, phenoxycyclopentyl, etc.
• aminocycloalkyl e.g., aminocyclobutyl
• hydroxycycloalkyl e.g., hydroxycyclohexyl
• arylcycloalkyl e.g., phenylcyclohexyl, phenylcyclobutyl, etc.
• alkylaminocycloalkyl e.g., methylaminocyclohexyl, methylaminocyclopentyl, etc.
• dialkylaminocycloalkyl e.g., diethylaminocyclohexyl, dimethylaminocyclobutyl, dipropylaminocyclooctyl, etc.
• arylaminocycloalkyl e.g., phenylaminocyclohexyl, diphenylaminocyclohexyl, N-phenyl-N- ethylaminocyclopentyl, N-phenyl-N- methylaminocyclohexyl, naphthylaminocyclopentyl, etc.
• nitrocycloalkyl e.g., nitrocyclobutyl, nitrocyclohexyl, nitrocyclopentyl, etc.
• cyanocycloalkyl e.g., cyanocyclohexyl, cyanocyclobutyl, cyanocyclopentyl, etc.
• halocycloalkyl e.g., chlorocyclohexyl, bromocyclopentyl, chlorocyclooctyl, etc.
• phenoxy, naphthoxy, etc. lower alkyl having one to eight carbon atoms, e.g., methyl, ethyl, propyl, butyl, etc.;
• a cycloalkenyl group having four to eight carbon atoms in the cyclic nucleus e.g., cyclohex-3-enyl, cyclopent-3-enyl, cyclobut-2-enyl, cyclohex-2- enyl, etc., including a substituted cycloalkenyl group such as a. alkoxycycloalkenyl e.g., ethoxycyclohex-3-enyl,
• aryloxycycloalkenyl e.g., phenoxycyclohex-3- enyl, phenoxycyclopent-3-enyl, naphthoxycyclohex-3-enyl, etc.
• aminocycloalkenyl e.g., aminocyclobut-Z-enyl, aminocyclohex-3-enyl, aminocycIopent-Z-enyl,
• hydroxycycloalkenyl e.g., hydroxycyclohex-3- enyl, hydroxycyclopent-Z-enyl, hydroxycyclobut-2-enyl, etc.
• arylcycloalkenyl e.g., phenylcyclohex-3-enyl
• alkylaminocycloalkenyl e.g., methylaminocyclohex-3-enyl, methylaminocyclopent--2-enyl, etc.
• dialkylaminocycloalkenyl e.g., diethylaminocyclohex-3-enyl, dimethyIaminocyclobut-Z-enyl, dipropyl'aminocyclooct-3-enyl, etc.
• arylaminocycloalkenyl e.g., phenylaminocyclohex-3-enyl, diphenylaminocyclohex-b 3-enyl, N-phenyl-N-ethylaminocyclopent-Z-enyl, etc.
• nitrocycloalkenyl e.g., nitrocycIobut-Z-enyl,ni trocyclohex-3-enyl, nktrocyclopent 2-enyl, etc.
• cyanocycloalkenyl e.g.,cyanocyclohex-3-enyl, cyanocyclobut-Z-enyl, cyanocyclopent-2-enyl, etc.
• halocycloalkenyl e.g., chlorocyclohex-3-enyl, bromocyclopent-2-enyl, chIorocyclooct-3-enyl, etc.
• Typical compounds which belong to the herein described general class of photoconductive materials include the following compounds listed in Table I below.
• Electrophotographic elements of the invention can be prepared with the photoconducting compounds of the invention in the usual manner, i.e., by blending a dispersion or solution of a photoconductive compound together with a binder, when necessary or desirable, and coating or forming a self-supporting layer with the photoconductor-containing material. Mixtures of the photoconductors described herein can be employed. Likewise, other photoconductors known in the art such as those described in Light Belgian Pat. No. 705,1 17 dated Apr. 16, 1968 can be combined with the present photoconductors. In addition, supplemental materials useful for changing the spectral sensitivity or electrophotosensitivity of the element can be added to the composition of the element when it is desirable to produce the characteristic effect of such materials.
• the photoconductive layers of the invention can also be sensitized by the addition of effective amounts of sensitizing compounds to exhibit improved electrophotosensitivity.
• Sensitizing compounds useful with the photoconductive compounds of the present invention can be selected from a wide variety of materials, including such materials as pyrylium dye salts including thiapyryliumdye salts and selenapyrylium dye salts disclosed in VanAllan et a].
• pyrylium dye salts including thiapyryliumdye salts and selenapyrylium dye salts disclosed in VanAllan et a].
• the sensitizers preferred for use with the compounds of this invention are selected from pyrylium salts including selenapyrylium salts and thiapyrylium salts, and cyanine dyes including carbocyanine dyes.
• sensitizing compound is employed with the binder and organic photoconductor to form a sensitized electrophotographic element
• Other methods of incorporating the sensitizer or the effect of the sensitizer may, however, be employed consistent with the practice of this invention.
• no sensitizing compound is required to give photoconductivity in the layers which contain the photoconducting substances, therefore, no sensitizer is required in a particular photoconductive layer.
• relatively minor amounts of sensitizing compound give substantial improvement in speed in such layers, the sensitizer is preferred.
• sensitizer that can be added to a photoconductorincorporating layer to give effective increases in speed
• concentration in any given case will vary with the specific photoconductor and sensitizing compound used.
• substantial speed gains can be obtained where an appropriate sensitizer is added in a concentration range from about 0.0001 to about 30 percent by weight based on the weight of the film-forming coating composition.
• a sensitizer is added to the coating composition in an amount by weight from about 0.005 to about 5.0
• Preferred binders for use in preparing the present photoconductive layers are film-forming, hydrophobic polymeric binders having fairly high dielectric strength which are good electrically insulating film-forming vehicles.
• Materials of this type comprise styrenebutadiene copolymers; silicone resins; styrene-alkyd resins; silicone-alkyd resins; soya-alkyd resins; poly(vinyl chloride); poly(vinylidene chloride); vinylidene chloride-acrylonitrile copolymers; poly(vinyl acetate); vinyl acetate-vinyl chloride copolymers; poly(vinyl acetals), such as poly(vinyl butyral); polyacrylic and methacrylic esters, such as poly(methyl methacrylate), poly(n-butyl methacrylate), poly(isobutyl methacrylate), etc.;polystyrene; nitrated polystyrene; polymethylst
• styrene-alkyd resins can be prepared according to the method described in Pat. Nos. 2,361,019 and 2,258,423.
• Suitable resins of the type contemplated for use in the photoconductive layers of the invention are sold under such tradenames as Vitel PE-101, Cymac, Piccopale 100, Saran F-220, Lexan and Lexan .145.
• Other types of binders which can be used in the photoconductive layers of the invention include such materials as paraffin, mineral waxes, etc.
• Solvents useful for preparing coating compositions with the photoconductors of the present invention can include a wide variety of organic solvents for the components of the coating composition.
• organic solvents for the components of the coating composition.
• benzene; toluene; acetone; 2-butanone; chlorinated hydrocarbons such as methylene chloride; ethylene chloride; and the like; ethers, such as tetrahydrofuran and the like, or mixtures of such solvents can advantageously be employed in the practice of this invention.
• the photoconductive substance is present in an amount equal to at least about 1 weight percent of the coating composition.
• the upper limit in the amount of photoconductive material present can be widely varied in accordance with usual practice. It is normally required that the photoconductive material be present in an amount ranging from about 1 weight percent of the coating composition to about 99 weight percent of the coating composition.
• a preferred weight range for the photoconductive material in the coating composition is from about 10 weight percent to about 60 weight percent.
• Coating thicknesses of the photoconductive composition on a support can vary widely. Normally, a wet coating thickness in the range of about 0.001 inch to about 0.01 inch is useful in the practice of the invention. A preferred range of coating thickness is from about 0.002 inch to about 0.006 inch before drying although such thicknesses can vary widely depending on the particular application desired for the electrophotographic element.
• Suitable supporting materials for the photoconductive layers of the present invention can include any of the electrically conducting supports, for example, various conducting papers; aluminum-paper laminates; metal foils, such as aluminum foil, zinc foil, etc.; metal plates, such as aluminum, copper, zinc, brass, and galvinized plates, vapor deposited metal layer such as silver, nickel or aluminum on conventional film supports such as cellulose acetate, poly(ethylene terephthalate),
• An especially useful conducting support can be prepared by coating a transparent film support material such as poly( ethylene terephthalate) with a layer containing a semiconductor dispersed in a resin.
• a suitable conducting coating can be prepared from the sodium salt of a carboxyester lactone of a maleic anhydridevinyl acetate copolymer, cuprous iodide and the like.
• compositions of the present invention can be employed in photoconductive elements useful in any of the well known electrophotographic processes which require photoconductive layers.
• One such process is the xerographic process.
• an electrophotographic element held in the dark is given a blanket positive or negative electrostatic charge as desired, by placing it under a coronadischarge to give a uniform charge to the surface of the photoconductive layer.
• This charge is retained by the layer owing to the I means of a conventional exposure operation such as for example, by a contact-printing technique, or by lens projection of an image, or reflex or bireflex techniques and the like, to thereby form a latent electrostatic image in the photoconductive layer.
• Exposing the surface in this manner forms a pattern of electrostatic charge by virtue of the fact that light energy striking the photoconductor causes the electrostatic charge in the light struck areas to be conducted away from the surface in proportion to the illuminance on a particular area.
• the charge pattern produced by exposure is then developed or transferred to another surface and developed there, i.e., either the charge or uncharged areas are rendered visible, by treatment with a medium comprising electrostatically responsive particles having optical density.
• the developing electrostatically responsive particles can be in the form of a dust, or powder and generally comprise a pigment in a resinous carrier called a toner.
• a preferred method of applying such a toner to a latent electrostatic image for solid area development is by the use of a magnetic brush. Methods of forming and using a magnetic brush toner applicator are described in the following U.S. Pat. Nos.
• Liquid development of the latent electrostatic image may also be used.
• liquid development the developing particles are carried to the image-bearing surface in an electrically insulating liquid carrier.
• Methods of development of this type are widely known and have been described in the patent literature, for example, U.S. Pat. No. 2,297,691 and in Australian Pat. No. 212,315.
• dry developing processes the most widely used method of obtaining a permanent record is achieved by selecting a developing particle which has as one of its components a low-melting resin.
• Heating the powder image then causes the resin to melt or fuse into or on the element.
• the powder is, therefore, caused to adhere permanently to the surface of the photoconductive layer.
• a transfer of the charge image or powder image formed on the photoconductive layer can be made to a second support such as paper which wouldthen become the final print after developing and fusing or fusing respectively.
• compositions of the present invention can be used in electrophotographic elements having many structural variations.
• the photoconductive composition can be coated in the form of single layers or multiple layers on a suitable opaque or transparent conducting support.
• the layers can be contiguous or spaced having layers of insulating material or other photoconductive material between layers or overcoated or interposed between the photoconduc tive layer or sensitizing layer and the conducting layer.
• . 1t is also possible to ad ust the position of the support and the conducting layer by placing a photoconductor layer over a support and coating the exposed face of the support or the exposed or overcoated face of the photoconductor with a conducting layer. Configurations differing from those contained in the examples can be useful or even preferred for the same or different application for the electrophotographic element.
• EXAMPLE 1 The following composition is sheared ina Waring Blendor for 30 minutes at room temperature.
• Binder Lexan l45/(tradename of I General Electric Company for a po1y(4,4-isopropylidenediphenylene Aphotoconductor (0.25 g.) is then dissolved in the resultant heterogeneous mixture which is then coated at 0.004-inch wet thickness on a poly(ethyleneterephthalate) support which had been precoated with an evaporated nickel conducting layer. The element is then dried at F.
• Several elements are prepared in this manner using various photoconductors of this invention. These electrophotographic elements are charged under a positive corona source until the surface potentials, as measured by en electrometer probe, reach about 600 volts. They are then subjected to exposure from behind a stepped density gray scale to a 3,000K. tungsten source.
• the exposure causes reduction of the surface'potentials of the elements under each step of the gray scale from their initial potential, V to some lower potential, V whose exact value depends on the actual amount of exposure in meter-candle-seconds received by the areas.
• the results of the measurements are plotted on a graph of surface potential V vs. log exposure for each step.
• the toe speed is the numerical expression of 10 multiplied by the reciprocal of the exposure in meter-candle-secondsrequired to reduce the 600 volt charged surface potential to volts.
• the speeds for the various photoconductors used are set forth in the following Table II.
• EXAMPLE III Another comparison is made using 1,l-bis(4-N,N-diethylamino-2-methylphenyl)methane as the photoconductor. The speed is determined in the same manner as Example I and is found to be 380.
• EXAMPLE V Coating dopes are prepared in the manner described in Example I using the materials set forth therein.
• the photoconductors employed are compounds I-XXI in Table I.
• the surface of each of the photoconductive layers so prepared is charged to a potential of about +600 volts under a corona charger.
• the layer is then covered with a transparent sheet bearing a pattern of opaque andlight transmitting areas and exposed to the radiation from an incandescent lamp with an illumination intensity of about 75 meter-candles for 12 seconds.
• the resulting electrostatic latent image is developed in the usual manner by cascading over the surface of the layer a mixture of negatively charged black thermoplastic toner particles on glass beads functioning as carriers for the toner particles. A good reproduction of the pattern results in each instance. Similar results are obtained using a liquid developer.
• the photoconducting compounds of this invention can generally be prepared by synthesis familiar to those skilled in the art.
• EXAMPLE X ganic precipitate is extracted into ether.
• the ether is evaporated off and the residue is steam distilled to remove unreacted N,N-diethylaniline.
• the organic residue is extracted into ether, dried (Na CO and concentrated by solvent evaporation.
• the residue is recrystallized from ethanol to give 180 g. of product, m.p. 70-71.
• the aqueous EXAMPLE xn Bis(4 N,N-diethyla'minophenyl)cyclohex-3- enylmethane, X1
• a mixture of 3-cyclohexenylcarboxaldehyde (1 mo] e), N,N-diethylaniline (2.0 moles), concentrated hy- "drochloric acid (100 mls.) and ethanol (15 mls.) is refluxed and then poured into water, made acid with hydrochloric acid and extracted with methylene chloride.
• the aqueous layer is made basic with sodium hydroxide.
• the organic precipitate solidifies and is filtered off, dried and crystallized from 2-rnethoxyethanol with charcoal treatment and hot filtration.
• the product is crystallized again from the same solvent to give 225 g. of material m.p. 137 l38. Analysis.
• An electrophotographic element comprising a supwherein:
• R R R and R are each lower alkyl groups having one to 18 carbon atoms, R and R are each selected from the group consisting of ahalogen atom, a hydrogen atom, an alkoxy group, and a lower aklyl group having one to 18 carbon atoms and R is selected from the group consisting of a lower alkyl group having one to 18 carbon atoms, a cycloalkyl group. having-four to eight carbon atoms and a cycloalkenyl group having four to eight carbon atoms.
• i I 7 The electrophotographic element as defined in claim 6 wherein said photoconductive composition contains a-sensitizer for said photoconductor.
• An electrophotographic element comprising a support having coated thereon a photoconductive composition comprising a. from about 10 to about 60 percent by weight based on said photoconductive composition of l,l-bis(4- N,N-diethylaminophenyl)-2-methylpropane as the organic photoconductor,
• An electrophotographic element comprising a support having coated thereon a photoconductive compoc. 0.005 percent to about 5 percent by weight based 6 on said photoconductive composition of a sensitizer for said photoconductive composition.
• An electrophotographic element comprising a support having coated thereon a photoconductive composition comprising a. from about 10 to about 60 percent by weight based on said photoconductive composition of 1,1-bis(4- N,N-diethylamino-2-methylphenyl )cyclohexylmethane, a b. a film-forming polymeric binder for said photoconductor and c. 0.005 percent to about 5 percent by weight based I on said photoconductive composition of a sensitizer for said photoconductive composition.
• An electrophotographic element comprising a support having coated thereon a photoconductive composition comprising a. from about 10 to about 60 percent by weight based on said photoconductive composition of l,l-bis(4- N,N-diethylamino-Z-methylphenyl)-2- rnethylpropane,
• An electrophotographic element comprising a support having coated thereon a photoconductive composition comprising i a. from about 10 to about 60 percent by weight based on said photoconductive composition of l,l-bis(4- N,N-diethylamino -2 methylphenyl)heptane,
• a photoconductive composition comprising a polymeric film-forming binder and a photoconductor selected from the group consisting of (a) alkylbis(N,N- dialkylaminoaryl)methane, (b) cycloalkylbis(N,N-
• dialkylaminoaryl)methane (c) cycloalkenylbis(N,N-dialkylaminoaryl)methane.
• a photoconductive composition comprising a polymeric film-forming binder and an organic photoconductor having the formula wherein:
• R R R and R are each lower alkyl groups having one to 18 carbon atoms, R and R are each selected from the group consisting of a halogen atom, a hydrogen atom, an alkoxy LII 16.
• said photoconductive element has a photoconductive layer comprising a compound selected from the group consisting of (a) alkylbis( N ,N- (dialkylaminoaryl)methane, (b) cycloalkylbis(N,N- dialkylaminoaryl)methane and (c) cycloalkenylbis(N,N-dialkylaminoaryl)methane.

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• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Health & Medical Sciences (AREA)
• Emergency Medicine (AREA)
• Photoreceptors In Electrophotography (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Priority Applications (7)

Applications Claiming Priority (1)

Publications (1)

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ID=25338561

Family Applications (1)

Country Status (7)

Cited By (141)

Families Citing this family (6)

• 0
  • BE BE756375D patent/BE756375A/fr unknown
• 1969
  • 1969-09-30 US US00862466A patent/US3820989A/en not_active Expired - Lifetime
• 1970
  • 1970-08-07 CA CA090220A patent/CA929015A/en not_active Expired
  • 1970-09-21 FR FR7034124A patent/FR2062429A5/fr not_active Expired
  • 1970-09-23 DE DE2046914A patent/DE2046914C3/de not_active Expired
  • 1970-09-24 GB GB4555770A patent/GB1319278A/en not_active Expired
  • 1970-09-30 JP JP45085146A patent/JPS4839177B1/ja active Pending

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